Palladium-Catalyzed Arylation of Aryl Sulfenate Anions with Aryl Bromides under Mild Conditions: Synthesis of Diaryl Sulfoxides

Organic Letters

Volumn 18, Issue 5, 2016, Pages 972-975

  Jiang, Hui ^a,b   Jia, Tiezheng ^b   Zhang, Mengnan ^b   Walsh, Patrick J ^b  

^a CHINA AGRICULTURAL UNIVERSITY   (China)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84960157010     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b00073     Document Type: Article

References (58)

1. Dini, I.; Tenore, G. C.; Dini, A. J. Nat. Prod. 2008, 71, 2036 10.1021/np800237w
2. El-Aasr, M.; Fujiwara, Y.; Takeya, T.; Tsukamoto, S.; Ono, M.; Nakamo, D.; Okawa, M.; Kinjo, J.; Yoshimitsu, H.; Nohara, T. J. Nat. Prod. 2010, 73, 1306 10.1021/np100105u
3. Wyche, T. P.; Piotrowski, J. S.; Hou, Y.; Braun, D.; Deshpande, R.; McIlwain, S.; Ong, I. M.; Myers, C. L.; Guzei, I. A.; Westler, W. M.; Andes, D. R.; Bugni, T. S. Angew. Chem., Int. Ed. 2014, 53, 11583 10.1002/anie.201405990
4. Nohara, T.; Fujiwara, Y.; Komota, Y.; Kondo, Y.; Saku, T.; Yamaguchi, K.; Komohara, Y.; Takeya, M. Chem. Pharm. Bull. 2015, 63, 117 10.1248/cpb.c14-00538
5. Rinehart, K. L.; Sakai, R. US2004/59112 A1, 2004.
6. Amira Pharmaceuticals, Inc. US/2010/4331 A1, 2010.
7. Amira Pharmaceuticals, Inc. Hutchinson, J. H.; Seiders, T. J.; Arruda, J. M.; Roppe, J. R. WO2010/42652 A2, 2010.
8. Combinatorx (Singapore) Pte. Ltd. US2010/9970 A1, 2010.
9. ACHAOGEN, Inc. WO2009/137130A2, 2009.
10. Astra Aktiebolag. U.S. Patent US5877192 A, 1998.
11. Laboratoire L. Lafon. U.S. Patent US4927855A, 1990.
12. Trost, B. M.; Rao, M. Angew. Chem., Int. Ed. 2015, 54, 5026 10.1002/anie.201411073
13. Mellah, M.; Voituriez, A.; Schulz, E. Chem. Rev. 2007, 107, 5133 10.1021/cr068440h
14. Trost, B. M.; Ryan, M. C.; Rao, M.; Markovic, T. Z. J. Am. Chem. Soc. 2014, 136, 17422 10.1021/ja510968h
15. Stang, E. M.; White, M. C. J. Am. Chem. Soc. 2011, 133, 14892 10.1021/ja2059704
16. Dornan, P. K.; Leung, P. L.; Dong, V. M. Tetrahedron 2011, 67, 4378 10.1016/j.tet.2011.02.023
17. Chen, J.; Chen, J.; Lang, F.; Zhang, X.; Cun, L.; Zhu, J.; Deng, J.; Liao, J. J. Am. Chem. Soc. 2010, 132, 4552 10.1021/ja1005477
18. Wojaczyńska, E.; Wojaczyński, J. Chem. Rev. 2010, 110, 4303 10.1021/cr900147h
19. O'Mahony, G. E.; Kelly, P.; Lawrence, S. E.; Maguire, A. R. ARKIVOC 2011, 1, 1 10.1002/chin.201138248
20. Bolm, C. Coord. Chem. Rev. 2003, 237, 245 10.1016/S0010-8545(02)00249-7
21. O'Donnell, J. S.; Schwan, A. L. J. Sulfur Chem. 2004, 25, 183 10.1080/1741599042000220761
22. Maitro, G.; Prestat, G.; Madec, D.; Poli, G. Tetrahedron: Asymmetry 2010, 21, 1075 10.1016/j.tetasy.2010.05.035
23. Schwan, A. L.; Söderman, S. C. Phosphorus, Sulfur Silicon Relat. Elem. 2013, 188, 275 10.1080/10426507.2012.729116
24. Zhang, M.; Jia, T.; Yin, H.; Carroll, P. J.; Schelter, E. J.; Walsh, P. J. Angew. Chem., Int. Ed. 2014, 53, 10755 10.1002/anie.201405996
25. Zhang, M.; Jia, T.; Wang, C. Y.; Walsh, P. J. J. Am. Chem. Soc. 2015, 137, 10346 10.1021/jacs.5b06137
26. Zhang, M.; Jia, T.; Sagamanova, I. K.; Pericas, M. A.; Walsh, P. J. Org. Lett. 2015, 17, 1164 10.1021/acs.orglett.5b00117
27. Zong, L.; Ban, X.; Kee, C. W.; Tan, C. H. Angew. Chem., Int. Ed. 2014, 53, 11849 10.1002/anie.201407512
28. Aversa, M. C.; Bonaccorsi, P.; Madec, D.; Prestat, G.; Poli, G. The Fabulous Destiny of Sulfenic Acids. In Innovative Catalysis in Organic Synthesis: Oxidation, Hydrogenation, and. C-X Bond Fanning Reactions; Andersson, P. G., Ed.; Wiley-VCH, 2012.
29. Maitro, G.; Vogel, S.; Prestat, G.; Madec, D.; Poli, G. Org. Lett. 2006, 8, 5951 10.1021/ol062315a
30. Maitro, G.; Vogel, S.; Sadaoui, M.; Prestat, G.; Madec, D.; Poli, G. Org. Lett. 2007, 9, 5493 10.1021/ol702343g
31. Bernoud, E.; Le Duc, G.; Bantreil, X.; Prestat, G.; Madec, D.; Poli, G. Org. Lett. 2010, 12, 320 10.1021/ol902620t
32. Gelat, F.; Lohier, J.-F.; Gaumont, A.-C.; Perrio, S. Adv. Synth. Catal. 2015, 357, 2011 10.1002/adsc.201500368
33. Izquierdo, F.; Chartoire, A.; Nolan, S. P. ACS Catal. 2013, 3, 2190 10.1021/cs400533e
34. Jia, T.; Bellomo, A.; Montel, S.; Zhang, M.; El Baina, K.; Zheng, B.; Walsh, P. J. Angew. Chem., Int. Ed. 2014, 53, 260 10.1002/anie.201307172
35. Jia, T.; Zhang, M.; Sagamanova, I. K.; Wang, C. Y.; Walsh, P. J. Org. Lett. 2015, 17, 1168 10.1021/acs.orglett.5b00092
36. Foucoin, F.; Caupène, C.; Lohier, J.-F.; de Oliveira Santos, J. S.; Perrio, S.; Metzner, P. Synthesis 2007, 2007, 1315 10.1055/s-2007-966017
37. Soderman, S. C.; Schwan, A. L. Org. Lett. 2011, 13, 4192 10.1021/ol201508e
38. Jia, T.; Bellomo, A.; EL Baina, K.; Dreher, S. D.; Walsh, P. J. J. Am. Chem. Soc. 2013, 135, 3740 10.1021/ja4009776
39. Field, L. Synthesis 1972, 1972, 101 10.1055/s-1972-21838
40. Field, L. Synthesis 1978, 1978, 713 10.1055/s-1978-24870
41. Trost, B. M.; Salzmann, T. N.; Hiroi, K. J. Am. Chem. Soc. 1976, 98, 4887 10.1021/ja00432a034
42. Trost, B. M. Acc. Chem. Res. 1978, 11, 453 10.1021/ar50132a004
43. Trost, B. M. Chem. Rev. 1978, 78, 363 10.1021/cr60314a002
44. Cubbage, J. W.; Guo, Y.; McCulla, R. D.; Jenks, W. S. J. Org. Chem. 2001, 66, 8722 10.1021/jo0160625
45. Aversa, M. C.; Barattucci, A.; Bilardo, M. C.; Bonaccorsi, P.; Giannetto, P. Synthesis 2003, 2241 10.1055/s-2003-41076
46. Latorre, A.; López, I.; Ramírez, V.; Rodríguez, S.; Izquierdo, J.; González, F. V.; Vicent, C. J. Org. Chem. 2012, 77, 5191 10.1021/jo300699w
47. Jia, T.; Zhang, M.; Jiang, H.; Wang, C. Y.; Walsh, P. J. J. Am. Chem. Soc. 2015, 137, 13887 10.1021/jacs.5b08117
48. Chambert, S.; Désiré, J.; Décout, J.-L. Synthesis 2002, 2319 10.1055/s-2002-35231
49. Oida, T.; Ohnishi, A.; Schimamaki, T.; Hayashi, Y.; Taniomoto, S. Bull. Chem. Soc. Jpn. 1991, 64, 702 10.1246/bcsj.64.702
50. Oida, T.; Nakamura, M.; Takashima, Y.; Hayashi, Y. Bull. Inst. Chem. Res. Kyoto Univ. 1992, 70, 295
51. Schwan, A. L.; Dufault, R. Tetrahedron Lett. 1992, 33, 3973 10.1016/0040-4039(92)88076-H
52. Schwan, A. L.; Strickler, R. R.; Dunn-Dufault, R.; Brillon, D. Eur. J. Org. Chem. 2001, 2001, 1643 10.1002/1099-0690(200105)2001:9<1643::AID-EJOC1643>3.3.CO;2-D
53. Molander, G. A.; Ryu, D. W.; Hosseini-Sarvari, M.; Devulapally, R.; Seapy, D. G. J. Org. Chem. 2013, 78, 6648 10.1021/jo4009589
54. Anderson, K. W.; Buchwald, S. L. Angew. Chem., Int. Ed. 2005, 44, 6173 10.1002/anie.200502017
55. Surry, D. S.; Buchwald, S. L. Chem. Sci. 2010, 1, 13 10.1039/c0sc00107d
56. Surry, D. S.; Buchwald, S. L. Chem. Sci. 2011, 2, 27 10.1039/C0SC00331J
57. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534 10.1021/ar800098p
58. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054 10.1021/cr8002505